Yeah, anyone who spends $100k on an ICE is... insane
But yeah, $1k (or $1.3k on lower Golf models) for the Dynaudio isn't bad considering...

As for your portable setup, the Sony MP3 players are alright, but I prefer the Sansa Clip+. It has better gapless support, great sound quality, has 8GB plus the ability to put a 32GB MicroSDHC card in it, and if you want, the ability to flash it with Rockbox. And costs less than the Sony

As for the earphohnes... ewww. Can't believe you can post a thread like this and then use them!
Bite the bullet, and look into Pro Music | JHAudio.com
Made specifically for your ears, they're comfortable enough to wear all day, or even sleep in. They can sound as good as you want to spend. Best of all, they're serviceable, and the cables are user replaceable. So they'd easily last a decade or more. Not recommended for kids or teenagers though, only for adults who have finished growing.